Cyclic tetrapeptides via the ring contraction strategy: chemical techniques useful for their identification
Organic & Biomolecular Chemistry2008Vol. 6(8), pp. 1386–1386
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Douglas A. Horton, Gregory T. Bourne, Justin F. Coughlan, Sonya M. Kaiser, Carolyn Jacobs, Alun Jones, Andreas Rühmann, Jill Y. Turner, Mark L. Smythe
Abstract
Cyclic tetrapeptides are a class of natural products that have been shown to have broad ranging biological activities and good pharmacokinetic properties. In order to synthesise these highly strained compounds a ring contraction strategy had previously been reported. This strategy was further optimised and a suite of techniques, including the Edman degradation and mass spectrometry/mass spectrometry, were developed to enable characterisation of cyclic tetrapeptide isomers. An NMR solution structure of a cyclic tetrapeptide was also generated. To illustrate the success of this strategy a library of cyclic tetrapeptides was synthesised.
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